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An efficient synthesis of New chiral oxazolines

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Abstract

Several new chiral oxazolines were prepared conveniently in good to high yields using a two-step synthesis involving formation of an optically active amide, in situ conversion of the amide into tosylate (OTs) and finally ring closing reaction under MW irradiation (800 W) in solvent free condition. A comparison of these results with those obtained from the ring closing reaction under classical conditions was also made.

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Refrences

  1. [1] a)

    A. Saeed, D.W. Young, Tetrahedron 48 (1992) 2507

  2. b)

    J. Shoji, H. Hinoo, T. Haltori, K. Kirooka, Y. Kimura, T. Yoshida, J. Antibiot. 42 (1988) 1460.

  3. [2]

    X.-M. Zhang, H.-L. Zhang, W.-Q. Lin, L.-Z. Gong, A.- Q. Mi, X. Cui, Y.-Z. Jiang, K.-B. Yu, J. Org. Chem. 68 (2003) 4322.

  4. [3] a)

    T.G. Gant, A.I. Meyers, Tetrahedron 50 (1994) 2297

  5. b)

    A.K. Ghosh, P. Mathivanan, J. Gappiello, Tetrahedron: Asymmetry 9 (1998) 1.

  6. [4] a)

    B.S. Davidson, Chem. Rev. 93 (1993) 1771

  7. b)

    J.P. Michael, G. Pattenden, Angew. Chem., Int. Ed. Engl. 32 (1993) 1

  8. c)

    H. Sone, H. Kigoshi, K. Yamada, Tetrahedron 53 (1997) 8149

  9. d)

    A. Rudi, M. Aknin, E.M. Gaydou, Y. Kashman, Tetrahedron 54 (1998) 13203

  10. e)

    C.D.J. Boden, M. Norley, G.J. Pattenden, J. Chem. Soc., Perkin Trans. 1 (2000) 883 and references cited therein.

  11. [5]

    J.A. Frump, Chem. Rev. 71 (1971) 483.

  12. [6] a)

    J.A. Frump, Chem. Rev. 71 (1971) 483

  13. b)

    A.I. Meyers, E.D. Mihelich, Angew. Chem., Int. Ed. Engl. 15 (1976) 270

  14. c)

    M. Reuman, A.I. Meyers, Tetrahedron 41 (1985) 837

  15. d)

    T.G. Gant, A.I. Meyers, Tetrahedron 50 (1994) 2297

  16. e)

    D.J. Ager, I. Prakash, D.R. Schaad, Chem. Rev. 96 (1996) 835.

  17. [7]

    B. Colman, S.E. de Sousa, P. O’Brien, T.D. Towers, W. Watson, Tetrahedron: Asymmetry 10 (1999) 4175 and references cited therein.

  18. [8] a)

    J.A. Frump, Chem. Rev. 71 (1971) 483

  19. b)

    A.I. Meyers, E.D. Michelich, Angew. Chem. (1976) 321.

  20. [9]

    R. Sharma, S.K. Vadivel, R.I. Duclos Jr., A. Makriyannis, Tetrahedron Lett. 50 (2009) 5780.

  21. [10]

    H. Wenker, J. Am. Chem. Soc. 57 (1935) 1079.

  22. [11]

    H. Vorbruggen, K. Krolikiewicz, Tetrahedron 49 (1993) 9353.

  23. [12]

    H. Vorbruggen, K. Krolikiewicz, Tetrahedron Lett. 22 (1981) 4471.

  24. [13]

    K. Kamata, I. Agata, J. Org. Chem. 63 (1998) 3113.

  25. [14] a)

    C. Bolm, K. Weickhardt, M. Zehnder, T. Ranff, Chem. Ber. 124 (1991) 1173

  26. b)

    D.S. Clarke, R. Wood, Synth. Commun. 26 (1996) 1335.

  27. [15]

    B. Oussaid, J. Berlan, M. Souflaoui, B. Garrigues, Synth. Commun. 25 (1995) 659.

  28. [16]

    A.R. Katritzky, C. Cai, K. Suzuki, S.K. Singh, J. Org. Chem. 69 (2004) 811.

  29. [17] a)

    P. Wipf, C.P. Miller, Tetrahedron Lett. 33 (1992) 907

  30. b)

    P. Wipf, S. Venkatraman, Tetrahedron Lett. 37 (1996) 4659.

  31. [18]

    A.J. Phillips, Y. Uto, P. Wipf, M.J. Reno, D.R. Williams, Org. Lett. 2 (2000) 1165.

  32. [19]

    P. Wipf, C.P. Miller, Tetrahedron Lett. 33 (1992) 6267.

  33. [20]

    M.C. Pirrung, L.N. Tumey, A.L. McClerren, C.R.H. Raetz, J. Am. Chem. Soc. 125 (2003) 1575.

  34. [21] a)

    M. Nikpassand, M. Mamaghani, F. Shirini, K. Tabatabaeian, Ultrason. Sonochem. 17 (2010) 301

  35. b)

    M. Nikpassand, M. Mamaghani, K. Tabatabaeian, M. Kupaei Abiazi, Mol. Divers. 13 (2009) 389

  36. c)

    M. Mamaghani, S. Dastmard, ARKIVOC, ii (2009) 168

  37. d)

    K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, A. Khorshidi, Catal. Commun. 9 (2008) 416

  38. e)

    K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, A. Khorshidi, J. Mol. Catal. A 270 (2007) 112

  39. f)

    M. Mamaghani, K. Tabatabaeian, M. Mirzaeinejad, M. Nikpassand, J. Iranian. Chem. Soc. 3 (2006) 89.

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Correspondence to M. Mamaghani.

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Mamaghani, M., Mahmoodi, N.O. & Ghasemi, S.F. An efficient synthesis of New chiral oxazolines. JICS 7, 972–977 (2010). https://doi.org/10.1007/BF03246093

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Keywords

  • Oxazoline
  • Chiral
  • Microwave
  • Chiral amide
  • Ring closing
  • Solvent free